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Synlett 1992; 1992(9): 703-705
DOI: 10.1055/s-1992-21459
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Synthesis of the C26-C37 Fragment of Calyculin A Having Natural Configuration

Fumiaki Yokokawa* , Yasumasa Hamada, Takayuki Shioiri
  • *Faculty of Pharmaceutical Sciences, Nagoya City University, Tanabe-dori, Mizuho-ku, Nagoya 467, Japan
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Publication Date:
08 March 2002 (online)

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An efficient synthesis of the C33-C37 fragment (methyl 4-benzyloxycarbonylamino-2,3-isopropylidenedioxy-5-methoxypentanoate, 3) of calyculin A (1) has been accomplished from (S)-serine using osmium tetroxide mediated dihydroxylation of the Z-olefin. The C26-C37 fragment 2 has been synthesized by coupling of the C33-C37 fragment 3 with the oxazole part (N3-C26 part) 4 by N,N-dimethylation.

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